Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I):

##STR00001##

[In the formulae, formula -A.sup.1- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A.sup.2- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I):

##STR00001##

[In the formulae, formula -A.sup.1- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A.sup.2- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I):

##STR00001##

[In the formulae, formula -A.sup.1- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A.sup.2- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1):

##STR00001##

wherein in formula (1), n represents 8, 9, 10, 11 or 12,
is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.

The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1):

##STR00001##

wherein in formula (1), n represents 8, 9, 10, 11 or 12,
is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid,
with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO.sub.4 and is preferably iron(III) nitrate.

The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1): ##STR00001##
wherein in formula (1), n represents 8, 9, 10, 11 or 12,
is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.